Isomerization and ring-closing metathesis for the synthesis of 6-, 7- and 8-membered benzo- and pyrido-fused N,N-, N,O- and N,S-heterocycles |
| |
Authors: | Willem AL van Otterlo |
| |
Institution: | Molecular Sciences Institute, School of Chemistry, University of the Witwatersrand, PO Wits, 2050 Johannesburg, South Africa |
| |
Abstract: | An isomerization-ring-closing metathesis (RCM) strategy afforded N-substituted 4H-1,4-benzoxazines from the protected N-allyl-2-(allyloxy)anilines. In addition, RCM was used to synthesize the N-substituted, 8-membered benzo-fused heterocycles from the respective diallyl compounds: 1,2,5,6-tetrahydro-1,6-benzodiazocine, 5,6-dihydro-2H-1,6-benzoxazocine, 5,6,9,10-tetrahydropyrido2,3-b]1,4]diazocine and 5,6-dihydro-2H-1,6-benzothiazocine 1,1-dioxide. The isomerization-RCM approach also afforded the 7-membered ring system, 2,5-dihydro-1,5-benzothiazepine 1,1-dioxide, from the protected N-allyl-2-(allylsulfonyl)aniline. Furthermore, the structure of 1,6-bis(4-methylphenyl)sulfonyl]-1,2,5,6-tetrahydro-1,6-benzodiazocine was confirmed by a single crystal X-ray determination. |
| |
Keywords: | Isomerization Ring-closing metathesis Benzo-fused heterocycles 1 4-Benzoxazines 1 6-Benzodiazocine 1 6-Benzoxazocine 1 6-Benzothiazocine 1 5-Benzothiazepine |
本文献已被 ScienceDirect 等数据库收录! |
|